Synthesis and ESI-MS alkali metal ion binding selectivities of cone, partial cone, and 1,3-alternate 1,3-bis(α-picolyloxy)-p-tert-butylcalix[4] arene crown-6 and 1,1′-binaphthalene-2,2′-diyl crown-6 conformers

Collection of Czechoslovak Chemical Communications

Volumn 69, Issue 5, 2004, Pages 1109-1125

  Ferguson, George ^a   Lough, Alan J ^b   Notti, Anna ^c   Pappalardo, Sebastiano ^d   Parisi, Melchiorre F ^c   Resnati, Giuseppe ^e  

^a UNIVERSITY OF GUELPH   (Canada)

^b UNIVERSITY OF TORONTO   (Canada)

^c UNIVERSITY OF MESSINA   (Italy)

^d UNIVERSITY OF CATANIA   (Italy)

^e POLITECNICO DI MILANO   (Italy)

Author keywords

Alkali metal ion selectivity; Biaryls; Binaphthalenes; Calixarenes; Crown compounds; Electrospray ionization mass spectrometry; Pyridine derivatives; X ray diffraction

Indexed keywords

1,1' BINAPHTHALENE 2,2' DIYL CROWN 6; 1,3 BIS(ALPHA PICOLYLOXY) 4 TERT BUTYLCALIX[4]ARENE CROWN 6; ALKALI METAL; CALIXARENE; CESIUM ION; METAL ION; NAPHTHALENE DERIVATIVE; SODIUM ION; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONFORMATION; REACTION ANALYSIS; SYNTHESIS;

EID: 3242799674     PISSN: 00100765     EISSN: None     Source Type: Journal    
DOI: 10.1135/cccc20041109     Document Type: Article

References (51)

1. a) Böhmer V.: Angew. Chem., Int. Ed. Engl. 1995, 34, 713;
2. b) Gutsche C. D. in: Calixarenes Revisited, Monographs in Supramolecular Chemistry (J. F. Stoddart, Ed.). The Royal Society of Chemistry, London 1998.
3. Rudkevich D. M. in: Calixarenes 2001 (Z. Asfari, V. Böhmer, J. Harrowfield and J. Vicens, Eds), Chap. 8, p. 155. Kluwer Academic, Dordrecht 2001.
4. Messina M. T., Metrangolo P., Pappalardo S., Parisi M. F., Pilati T., Resnati G.: Chem. Eur. J. 2000, 6, 3495.
5. Hassel O.: Science 1970, 170, 497;
6. b) Bent H. A.: Chem. Rev. 1968, 68, 587;
7. c) Legon A. C.: Angew. Chem., Int. Ed. 1999, 38, 2686.
8. a) Corradi E., Mille S. V., Messina M. T., Metrangolo P., Resnati G.: Angew. Chem., Int. Ed. 2000, 39, 1782;
9. b) Metrangolo P., Resnati G.: Chem. Eur. J. 2001, 7, 2511.
10. Metrangolo P., Panzeri W., Recupero F., Resnati G.: J. Fluorine Chem. 2002, 114, 27.
11. Liantonio R., Metrangolo P., Pilati T., Resnati G.: Cryst. Growth Des. 2003, 3, 355.
12. Vilar R.: Angew. Chem., Int. Ed. 2003, 42, 1460.
13. For a recent review see: Casnati A., Ungaro R., Asfari Z., Vicens J. in: Calixarenes 2001 (Z. Asfari, V. Böhmer, J. Harrowfield and J. Vicens, Eds), Chap. 20, p. 365. Kluwer Academic, Dordrecht 2001.
14. Arnaud-Neu F., Ferguson G., Fuangswasdi S., Notti A., Pappalardo S., Parisi M. F., Petringa A.: J. Org. Chem. 1998, 63, 7770.
15. a) Guardigli C., Liantonio R., Lorenza Mele M., Metrangolo P., Resnati G., Pilati T.: Supramol. Chem. 2003, 15, 177;
16. b) Liantonio R., Logothetis T. A., Messina M. T., Metrangolo P., De Santis A., Pilati T., Resnati G.: Collect. Czech. Chem. Commun. 2002, 67, 1373;
17. c) Liantonio R., Metrangolo P., Pilati T., Resnati G.: Acta Crystallogr., Sect. E 2002, 58, 575;
18. d) Messina M. T., Metrangolo P., Resnati G., Quici S., Manfredi A., Pilati T.: Supramol. Chem. 2001, 12, 405;
19. e) Bailey Walsh R., Padgett C. W., Metrangolo P., Resnati G., Hanks T. W., Pennington W. T.: Cryst. Growth Des. 2001, 1, 165.
20. a) Pappalardo S., Petringa A., Parisi M. F., Ferguson G.: Tetrahedron Lett. 1996, 37, 3907;
21. b) Ferguson G., Lough A. J., Notti A., Pappalardo S., Parisi M. F., Petringa A.: J. Org. Chem. 1998, 63, 9703;
22. c) Occhipinti S., Pappalardo S., Gattuso M., Notti A., Parisi M. F.: Recent Res. Dev. Org. Chem. 2000, 4, 361.
23. a) Yamamoto H., Sakaki T., Shinkai S.: Chem. Lett. 1994, 469;
24. b) For the preparation of 5a under different conditions, see: Chen X., Ji M., Fisher D. R., Wai C. M.: Inorg. Chem. 1999, 38, 5449, and references therein.
25. Spek A. L.: PLATON, Molecular Geometry and Graphics Program. September 1998 version. University of Utrecht, Utrecht 1998.
26. Andreetti G. D., Ori O., Ugozzoli F., Alfieri C., Pochini A., Ungaro R.: J. Inclusion Phenom. Mol. Recogn. Chem. 1988, 6, 523.
27. Bottino F., Pappalardo S.: J. Inclusion Phenom. Mol. Recogn. Chem. 1994, 19, 85; and references therein.
28. Jaime C., de Mendoza J., Prados P., Nieto P. M., Sánchez C.: J. Org. Chem. 1991, 56, 3372.
29. Pappalardo S.: New J. Chem. 1996, 20, 465; and references therein.
30. Nierengarten H., Leize E., Breuning E., Garcia A., Romero-Salguero F., Rojo J., Lehn J.-M., Van Dorsselaer A.: J. Mass Spectrom. 2002, 37, 56.
31. Sherman C. L., Brodbelt J. S.: Anal. Chem. 2003, 75, 1828.
32. a) Brodbelt J. S., Kempen E., Reyzer M.: Struct. Chem. 1999, 10, 213;
33. b) Blanda M. T., Farmer D. B., Brodbelt J. S., Goolsby B. J.: J. Am. Chem. Soc. 2000, 122, 1486, and references therein;
34. c) Allain F., Virelizier H., Moulin C., Jankowski C. K., Dozol J. F., Tabet J. C.: Spectroscopy 2000, 14, 127;
35. d) Reyzer M. L., Brodbelt J. S., Marchand A. P., Chen Z., Huang Z., Namboothiri I. N. N.: Int. J. Mass Spectrom. 2001, 204, 133;
36. e) Williams S., Blaira S. M., Brodbelt J. S., Huang X., Bartsch R. A.: Int. J. Mass Spectrom. 2001, 212, 389.
37. a) Ungaro R., Casnati A., Ugozzoli F., Pochini A., Dozol J.-F., Hill C., Rouquette H.: Angew. Chem., Int. Ed. Engl. 1994, 33, 1506;
38. b) Casnati A., Pochini A., Ungaro R., Ugozzoli F., Arnaud F., Fanni S., Schwing M.-J., Egberink R. J. M., de Jong F., Reinhoudt D. N.: J. Am. Chem. Soc. 1995, 117, 2767;
39. c) Sachleben R. A., Bryan J. C., Das G., Descazeaud T., Sun Y., Moyer B. A.: J. Inclusion Phenom. Mol. Recogn. Chem. 2002, 43, 55.
40. Cecille L. (Ed.): Radioactive Waste Management and Disposal. Elsevier, London, New York 1991.
41. a) Jankowski C. K., Allain F., Lamouroux C., Virelizier H., Moulin C., Tabet J.-C., Lamare V., Dozol J.-F.: Spectrosc. Lett. 2003, 36, 327;
42. b) Ghidini E., Ugozzoli F., Ungaro R., Harkema S., Abu El-Fadl A., Reinhoudt D. N.: J. Am. Chem. Soc. 1990, 112, 6979;
43. c) Alfieri C., Dradi E., Pochini A., Ungaro R., Andreetti G. D.: J. Chem. Soc., Chem. Commun. 1983, 1075.
44. Ouchi M., Inoue Y., Kanzaki T., Hakushi T.: J. Org. Chem. 1984, 49, 1408.
45. Kyba E. P., Gokel G. W., de Jong F., Koga K., Sousa L. R., Siegel M. G., Kaplan L., Dotsevi G., Sogah Y., Cram D. J.: J. Org. Chem. 1977, 42, 4173.
46. Gutsche C. D., Iqbal M.: Org. Synth. 1989, 68, 234.
47. a) Bottino F., Giunta L., Pappalardo S.: J. Org. Chem. 1989, 54, 5407;
48. b) Shinkai S., Otsuka T., Araki K., Matsuda T.: Bull. Chem. Soc. Jpn. 1989, 62, 4055.
49. The synthesis of the two enantiomers of 5b has recently been reported: Bitter I., Köszegi E., Grün A., Bakó P., Pál K., Grofcsik A., Kubinyi M., Balázs B., Tóth G.: Tetrahedron: Asymmetry 2003, 14, 1025.
50. Sheldrick G. M.: SHELXS97, Program for the Solution of Crystal Structures. University of Göttingen, Göttingen 1997.
51. Sheldrick G. M.: SHELXL97, Program for the Refinement of Crystal Structures. University of Göttingen, Göttingen 1997.